Water → HCID 59168954, compound

HRID 1444793Notes

Reaction equation

HRID 1444793 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[C:11]1[C:12](=[O:33])[O:13][C:14]2[C:19]([C:20]=1[CH2:21][CH2:22][O:23]C)=[CH:18][CH:17]=[C:16]([O:25][S:26]([C:29]([F:32])([F:31])[F:30])(=[O:28])=[O:27])[CH:15]=2.B(Br)(Br)Br.O.C(OCC)(=O)C>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:11]1[C:12](=[O:33])[O:13][C:14]2[C:19]([C:20]=1[CH2:21][CH2:22][OH:23])=[CH:18][CH:17]=[C:16]([O:25][S:26]([C:29]([F:31])([F:32])[F:30])(=[O:28])=[O:27])[CH:15]=2

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 11641654HCID 11641654, compound

Product 1

HCID 59168954HCID 59168954, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

Trifluoro-methanesulfonic acid 3-(2,4-dimethoxy-phenyl)-4-(2-methoxy-ethyl)-2-oxo-2H-chromen-7-yl ester (450 mg, 0.92 mol) was dissolved in CH2Cl2 (10 mL) at room temperature in a 200 ml round bottom flask. The reaction mixture was then cooled to −30° C., and BBr3 (1.8 ml) was added and the reaction mixture stirred at room temperature for 4 h. The reaction mixture was cooled to 0° C. and water (40 mL) was added, followed by ethyl acetate (50 mL). The reaction mixture was then poured into a separation funnel. The organic layer was separated and washed with water (1×40 ml) and brine (1×30 ml). The organic layer was dried over sodium sulfate and concentrated. The product was purified on silica gel eluted with 50%-100% ethyl acetate in hexanes to yield trifluoro-methanesulfonic acid 3-(2,4-dihydroxy-phenyl)-4-(2-hydroxy-ethyl)-2-oxo-2H-chromen-7-yl ester as a light yellow foam

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. additionThe reaction mixture was then poured into a separation funnel
  3. customThe organic layer was separated
  4. washwashed with water (1×40 ml) and brine (1×30 ml)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified on silica gel
  8. washeluted with 50%-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0a43f4b2d4274df989396703b4b694a3
Source dataset
uspto-grants-2010_02
Patent number
US07662975B2

Reaction notes

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